Is it better to deal with difficult or easy issues first?

In general, dealing with easier issues will build momentum, deepen the parties’ commitment to the process, and enable the parties to become familiar with each other’s negotiation and communication styles before hitting the tough stuff.

In some instances, however, you may want to deal with a more difficult issue as a threshold matter. If you cannot reach tentative agreement on the difficult issue(s), then you will not have wasted time on the smaller issues. It is also true that once the most difficult issue is resolved, smaller issues often fall more easily into place.